How do I get him back my relationship with him when he is confused between me and a new interest?

We were friends for 4 months and dated for 5 months, but I broke up with him twice before because I was insecure about our relationship. He started to date a new lady then one day when he saw me again he became confused. We were having a really great time but I was insecure about our relationship because he was much older. His friend warned him about getting serious with me because I'm 24 and he said he wouldn't. We broke up twice but we didn't stop communicating and it was mostly because it was accidental. I apologized both times for bringing it up because I was insecure. He was almost on the verge of falling for me and he asked what we were and I told him that I don't think he is ready to be my boyfriend. I started to give him time. He started dating another woman and then when he saw me again, his feelings stirred up. I told him how much I want to be with him and he is confused. We tried to talk about what went wrong with our relationship. And then he planned on breaking things off with me completely then when he saw me again he became confused. I use to be cold and shelled because I was pretty insecure. But now I'm showing him a new side and he is pleasantly surprised. He has only talked about me to her broadly but he let me know that he started seeing another woman. We did fool around and go on another date. I told him how much I want him to be mine and how much I miss him... but he is still confused on who to choose.

Updates:
So... I copied the exact words from the site and accidentally forwarded this to him. He was pretty chill about it but I'm probably going to give up on this relationship soon.

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  • tell him how you feel.

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